US4115557AExpiredUtility

Substituted pyridinyl O-alkyl phenyl/phosphonothioates and their use as pesticides

61
Assignee: DOW CHEMICAL COPriority: Jan 15, 1976Filed: Apr 18, 1977Granted: Sep 19, 1978
Est. expiryJan 15, 1996(expired)· nominal 20-yr term from priority
Inventors:Chester E. Pawloski
C07F 9/58A01N 57/24
61
PatentIndex Score
4
Cited by
2
References
68
Claims

Abstract

Substituted (2-)pyridinyl phosphonothioates are disclosed which are useful in the control of cotton leafworm larvae. The compounds are prepared by the reaction of selected substituted pyridinol and phosphonochloridothioate reactants.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
       1. A compound corresponding to the formula: ##STR8## wherein R is phenyl of phenyl being mono- or polysubstituted with bromo, chloro, fluoro or methyl; R 1  represents alkyl or 1 to 4 carbon atoms; and X 1 , X 2 , X 3  and X 4  each independently represent bromo, chloro, fluoro, trifluoromethyl or hydrogen, with the proviso that at least one of X 1 , X 2 , X 3  and X 4  is hydrogen; at least one of the others of X 1 , X 2 , X 3  and X 4  is other than hydrogen; with the added proviso that when X 1 , X 2  X 3  or X 4  is selected from bromo, chloro or fluoro, that no more than two of X 1 , X 2 , X 3  and X 4  can be the same. 
     
     
       2. A compound corresponding to claim 1 wherein R is phenyl and R 1  is methyl or ethyl. 
     
     
       3. The compound of claim 2 which is 0-(6-chloro-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       4. The compound of claim 2 which is 0-(6-fluoro-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       5. The compound of claim 2 which is 0-(6-fluoro-2-pyridinyl) 0-ethyl phenylphosphonothioate. 
     
     
       6. The compound of claim 2 which is 0-(6-chloro-2-pyridinyl) 0-ethyl phenylphosphonothioate. 
     
     
       7. The compound of claim 2 which is 0-(6-bromo-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       8. The compound of claim 2 which is 0-(6-trifluoromethyl)-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       9. The compound according to claim 2 which is 0-(5-bromo-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       10. The compound according to claim 2 which is 0-(5-chloro-2-pyridinyl) 0-ethyl phenylphosphonothioate. 
     
     
       11. The compound according to claim 2 which is 0-(5-chloro-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       12. The compound according to claim 2 which is 0-(4-chloro-2-pyridinyl) 0-ethyl phenylphosphonothioate. 
     
     
       13. The compound according to claim 2 which is 0-(3,5-dichloro-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       14. The compound according to claim 2 which is 0-(3,5-dichloro-2-pyridinyl) 0-ethyl phenylphosphonothioate. 
     
     
       15. The compound according to claim 2 which is 0-(3,5-dibromo-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       16. The compound according to claim 2 which is 0-(3,6-dichloro-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       17. The compound according to claim 2 which is 0-(4,6-dichloro-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       18. The compound according to claim 2 which is 0-(4,6-dichloro-2-pyridinyl) 0-ethyl phenylphosphonothioate. 
     
     
       19. The compound according to claim 2 which is 0-(3,6-dichloro-2-pyridinyl) 0-ethyl phenylphosphonothioate. 
     
     
       20. The compound according to claim 2 which is 0-(5-bromo-3,6-dichloro-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       21. The compound according to claim 2 which is 0-(3,5-dichloro-6-fluoro-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       22. The compound according to claim 2 which is 0-(6-bromo-3,5-dichloro-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       23. A composition comprising a pesticidally-effective amount of a compound of the formula: ##STR9## wherein R is phenyl or phenyl being mono- or polysubstituted with bromo, chloro, fluoro or methyl; R 1  represents alkyl of 1 to 4 carbon atoms; and X 1 , X 2 , X 3  and X 4  each independently represent bromo, chloro, fluoro, trifluoromethyl or hydrogen, with the proviso that at least one of X 1 , X 2 , X 3  and X 4  is hydrogen; at least one of the others of X 1 , X 2 , X 3  and X 4  is other than hydrogen; with the added proviso that when X 1 , X 2 , X 3  or X 4  is selected from bromo, chloro or fluoro, that no more than two of X 1 , X 2 , X 3  and X 4  can be the same. 
     
     
       24. A composition according to claim 23 wherein R is phenyl and R 1  is methyl or ethyl. 
     
     
       25. The composition of claim 24 wherein the compound is 0-(6-chloro-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       26. The composition of claim 24 wherein the compound is 0-(6-fluoro-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       27. The composition of claim 24 wherein the compound is 0-(6-fluoro-2-pyridinyl) 0-ethyl phenylphosphonothioate. 
     
     
       28. The composition of claim 24 wherein the compound is 0-(6-chloro-2-pyridinyl) 0-ethyl phenylphosphonothioate. 
     
     
       29. The composition of claim 24 wherein the compound is 0-(6-bromo-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       30. The composition of claim 24 wherein the compound is 0-(6-trifluoromethyl)-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       31. The composition of claim 24 wherein the compound is 0-(5-bromo-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       32. The composition of claim 24 wherein the compound is 0-(5-chloro-2-pyridinyl) 0-ethyl phenylphosphonothioate. 
     
     
       33. The composition of claim 24 wherein the compound is 0-(5-chloro-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       34. The composition of claim 24 wherein the compound is 0-(4-chloro-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       35. The composition according to claim 24 wherein the compound is 0-(3,5-dichloro-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       36. The composition according to claim 24 wherein the compound is 0-(3,5-dichloro-2-pyridinyl) 0-ethyl phenylphosphonothioate. 
     
     
       37. The composition according to claim 24 wherein the compound is 0-(3,5-dibromo-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       38. The composition according to claim 24 wherein the compound is 0-(3,6-dichloro-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       39. The composition according to claim 24 wherein the compound is 0-(3,6-dichloro-2-pyridinyl) 0-ethyl phenylphosphonothioate. 
     
     
       40. The composition according to claim 24 wherein the compound is 0-(4,6-dichloro-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       41. The composition according to claim 24 wherein the compound is 0-(4,6-dichloro-2-pyridinyl) 0-ethyl phenylphosphonothioate. 
     
     
       42. The composition according to claim 24 wherein the compound is 0-(5-bromo-3,6-dichloro-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       43. The composition according to claim 24 wherein the compound is 0-(3,5-dichloro-6-fluoro-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       44. The composition according to claim 24 wherein the compound is 0-(6-bromo-3,5-dichloro-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       45. The composition of claim 24 wherein the inert carrier is a solid. 
     
     
       46. The composition of claim 24 wherein the inert carrier is a liquid. 
     
     
       47. A method for controlling cotton leafworm larvae which comprises contacting said larvae and/or their habitats with a pesticidally-effective amount of composition containing as the active ingredient a compound corresponding to the formula: ##STR10## wherein R is phenyl or phenyl being mono- or polysubstituted with bromo, chloro, fluoro or methyl; R 1  represents alkyl of 1 to 4 carbon atoms; and X 1 , X 2 , X 3  and X 4  each independently represent bromo, chloro, fluoro, trifluoromethyl or hydrogen, with the proviso that at least one of X 1 , X 2 , X 3  and X 4  is is hydrogen; at least one of the others of X 1 , X 2 , X 3  and X 4  is other than hydrogen; with the added proviso that when X 1 , X 2 , X 3  or X 4  is selected from bromo, chloro or fluoro, that no more than two of X 1 , X 2 , X 3  and X 4  can be the same. 
     
     
       48. The method of claim 47 wherein R is phenyl and R 1  is methyl or ethyl. 
     
     
       49. The method of claim 48 wherein the compound is 0-(6-chloro-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       50. The method of claim 48 wherein the compound is 0-(6-fluoro-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       51. The method of claim 48 wherein the compound is 0-(6-fluoro-2-pyridinyl) 0-ethyl phenylphosphonothioate. 
     
     
       52. The method of claim 48 wherein the compound is 0-(6-chloro-2-pyridinyl) 0-ethyl phenylphosphonothioate. 
     
     
       53. The method of claim 48 wherein the compound is 0-(6-bromo-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       54. The method of claim 48 wherein the compound is 0-((6-trifluoromethyl)-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       55. The method of claim 48 wherein the compound is 0-(5-bromo-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       56. The method of claim 48 wherein the compound is 0-(5-chloro-2-pyridinyl) 0-ethyl phenylphosphonothioate. 
     
     
       57. The method of claim 48 wherein the compound is 0-(5-chloro-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       58. The method of claim 48 wherein the compound is 0-(4-chloro-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       59. The method according to claim 48 wherein the compound is 0-(3,5-dichloro-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       60. The method according to claim 48 wherein the compound is 0-(3,5-dichloro-2-pyridinyl) 0-ethyl phenylphosphonothioate. 
     
     
       61. The method according to claim 48 wherein the compound is 0-(3,5-dibromo-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       62. The method according to claim 48 wherein the compound is 0-(3,6-dichloro-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       63. The method according to claim 48 wherein the compound is 0-(3,6-dichloro-2-pyridinyl) 0-ethyl phenylphosphonothioate. 
     
     
       64. The method according to claim 48 wherein the compound is 0-(4,6-dichloro-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       65. The method according to claim 48 wherein the compound is 0-(4,6-dichloro-2-pyridinyl) 0-ethyl phenylphosphonothioate. 
     
     
       66. The method according to claim 48 wherein the compound is 0-(5-bromo-3,6-dichloro-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       67. The method according to claim 48 wherein the compound is 0-(3,5-dichloro-6-fluoro-2-pyridinyl) 0-methyl phenylphosphonothioate. 
     
     
       68. The method according to claim 48 wherein the compound is 0-(6-bromo-3,5-dichloro-2-pyridinyl) 0-methyl phenylphosphonothioate.

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